Nutritive compositions containing fatty substances

ABSTRACT

Food compositions having an added γ-linolenic acid component are provided for human and animal nutrition. The supplemented foods contain an oil extracted from pips of Ribes genus fruits containing at least 4% by weight of γ-linolenic acid. The oil is substantially free from waxes, odorous compounds, colorings and free fatty acids.

This application is a continuation application of application Ser. No.07/095,550 filed 09/11/87 which is a divisional application ofapplication Ser. No. 06/542,149, filed Oct. 14, 1983, now U.S. Pat. No.4,703,060, which in turn is a continuation-in-part of application Ser.No. 06/482,429, filed April 6, 1983, now abandoned. BACKGROUND OF THEINVENTION

1. Field of the Invention

This invention relates to nutritive compositions containing fattysubstances, and to a process for the preparation of said compositionsfrom fruits of the Ribes genus.

2. Description of Related Art

Most vegetable oils contain linoleic (6,9-octadecadienic) andα-linolenic (9,12,15-octadecatrienic) polyunsaturated fatty acids. Onlyoils of the seeds of hops (Humulus), of hemp (Cannabis), of borage(Borage) and of evening primrose (Oenothera) are known as containingγ-linolenic (6,9,12-octadecatrienic) acid, evening primrose being theonly available source at, moreover, a high price.

γ-Linolenic acid is an essential fatty acid which is metabolised by theorganism into prostaglandins via dihomo-γ-linolenic acid and arachidonicacid (5,8,11,14-eicosatetraenic), which is itself a constituent ofcellular membranes, whereas α-linolenic acid does not take part in thesame way in this metabolic process. The linoleic acid conversion intoγ-linolenic acid in the tissue is incomplete (4-20% compared to 90-98%for the conversion of γ-linolenic acid into arachidonic acid) and maynot even exist (for example in cats) in the case of the absence or theinactivation of the enzyme Δ-6-desaturase.

In effect, a lack of essential fatty acids results in a nutritionaldeficiency affecting all the metabolic processes which have beenmentioned above and which may result in biochemical disorders or inorganic lesions (for example coagulation disorders, dermatologicallesions, endocrinal complaints, myocardiac lesions, and hepatic,articular, neurological and mental disorders). Therefore, it is possibleto see the advantages provided by a supply of γ-linolenic acid for theprevention or for the treatment of these anomalies.

The possibility of using γ-linolenic acid and arachidonic acid astherapeutic and nutritional agents has been mentioned in, for exampleFrench Patents Nos. 2,197,605 and 1,603,383, γ-linolenic acid being of asynthetic origin or being extracted from the oil of evening primrose(Oenothera) or officinal borage (Borage officinalis) seeds.

Moreover, French Patent No. 2,255,055 relates to cosmetic orpharmaceutical compositions based on the oil of raspberry pips, theanti-inflammatory activity of which is mentioned, but with no indicationof the composition. Since the oil is preferably extracted usingchloroform (a polar solvent), the anti-inflammatory activity is probablydue to the presence of minor components. Moreover, analysis of this oilhas shown that it contained about 54% by weight of linoleic acid and 30%of a α-linolenic acid, but did not contain any γ-linolenic acid.

Finally, Hungarian Patent No. T 13226 states that the addition of a pulpor a crude oil extracted from paprika, tomato or redcurrant pips tocosmetic products or table oils would inhibit their oxidation. Theextraction, as it is described, does not allow the separation of theundesirable waxes and colourings in the products which are envisaged andthe composition of the extract is not mentioned.

SUMMARY OF THE INVENTION

Surprisingly, it has been found that oils of pips of fruit of the Ribesgenus contain an appreciable percentage, at least 4% by weight, ofγ-linolenic acid. Moreover, these pips are available in large quantitiesin the cakes resulting from squeezing fruit juices, from the productionof preserves and jellies or from fermentation musts resulting from theproduction of brandies, liqueurs and schnapps, by-products which havebeen used up until now as fuel or forage.

The present invention relates to nutritive compositions which containfrom 0.44% to 80% by weight of a fatty substance extracted from pips offruit of the Ribes genus containing at least 4% by weight of γ-linolenicacid which is practically free from odorous compounds, the free fattyacids, the colourings and the waxes of these fruits.

DESCRIPTION OF THE INVENTION

As used in the context of this invention, the term "nutritivecomposition" designates cosmetic, dermatological (corrective cosmetic)or topical (for example ophthalmic) compositions and dietetic foods orfood supplement, or pharmaceutical compositions for oral, enteral orparental nutrition.

According to the present invention, the fatty substances entering intothe nutritive composition originate in practice from blackcurrants(Ribes nigrum), redcurrants (Ribes rubrum), gooseberries (Ribesovacrispa or grossularia) or from hybrid fruits of these species. Ofcourse, a mixture of these fruits may be used.

The lipid content of the by-products mentioned above is from 12 to 30%by weight, depending on the starting material. For its part, the lipidphase contains from 4 to 19% by weight of γ-linolenic acid.

As an indication, the oil of the pips of these fruits comprisestriglycerides of the following fatty acids, by weight:

    ______________________________________                                                               Red                                                    Fatty Acids Blackcurrants                                                                            Currants   Gooseberries                                ______________________________________                                        C 16:0      6-7%       4-5%       7-8%                                        C 18:0      1-2%       1-2%       1-1%                                        C 18:1 cis   9-10%     14-15%     15-16%                                      C 18:1 trans                                                                              0.5%       0.5-1%     1-2%                                        C 18:2 ω 6                                                                          47-49%     41-42%     39-41%                                      C 18:3 ω 6                                                                          15-19%     4-5%       10-12%                                      C 18:3 ω 3                                                                          12-14%     29-31%     19-20%                                      C 18:4 ω 3                                                                          3-4%       2.5-3.5%   4-5%                                        ______________________________________                                    

Blackcurrant oil which is preferred due to its high content ofγ-linolenic acid also contains from 1 to 2% by weight of unsaponifiablesubstances, such as aliphatic alcohols, hydrocarbons, tocopherols,squalene, β-sitosterol, campesterol and Δ-7 stigmasterol. Its density is0.9215 g/cm³ (at 20° C.), and its viscosity is 28.3 centipoise (at 20°C.).

A cosmetic or dermatological composition may be presented in the form ofa fluid water-in-oil or oil-in-water emulsion (milk, lotion, shampoo,shaving foam, etc.,) or in the form of a thicker emulsion (cream, facepack), and it generally contains from 1 to 20% by weight of the fattysubstance mentioned above. It may essentially comprise an oil phase(balm, bath oil, etc.), containing up to 80% of the fatty substancementioned above, or it may have a predominant water phase (capillaryrinsing product, etc.). Finally, it may be essentially solid (make-upproducts, eye shadow, foundation, lipstick, etc.) and may contain from 1to 30% of the fatty substance mentioned above.

In addition to containing the fatty substance mentioned above, the fatphase of the composition may contain vegetable, animal, mineral orsynthetic oils, waxes, long chain alcohols and polymers which arepresently used in cosmetics.

If emulsions are concerned, the compositions contain from 1 to 20% byweight of emulsifiers.

Moreover, the compositions may contain colouring agents, perfumes,preservatives, pigments, lustrants, antioxidants and extenders.

Among the dietetic foods or food supplements which are envisaged, it ispossible to mention infants' milk and more particularly milk having thecomposition of mother's milk, sauces, mayonnaise and oils for salads. Inthese products, the fatty substances are compounded so that they providethe equivalent of γ-linolenic acid by weight based on the total weightof the nutritive product in an amount of from an amount which provides acomposition having a γ-linolenic acid content corresponding with theamount of γ-linolenic acid in human mother's milk, which such as in aninfant formula according to the invention is about [0.35] 0.08% byweight of γ-linolenic acid based on the total weight of the product, to2.5% by weight of γ-linolenic acid by weight, and the fatty substancesare compounded to represent from 0.44% [2] to 15% by weight. That is,such as with the fatty substance black-currant oil, the lower levelamount of fatty substances incorporated in a product by weight, such asan infant milk formula, may represent an amount of the fatty substances,as calculated from the table above, of from 0.44% to 0.56% based on theblack currant oil having a γ-linolenic acid content of from 19% to 15%,respectively. See also Example 18 in which black currant oil in anamount of 0.61% of the total weight of an infant formula prepared inaccordance with the present invention is utilized for providing therequisite amount of γ-linolenic acid thereby indicating that the oil hada γ-linolenic acid content of about 14%. Similarly, in the case ofgooseberry oil, the lower level of fatty substance by weight may becalculated as being from some 0.7% to 0.84% based on the gooseberry oilhaving a γ-linolenic acid content of from 12% to 10%, respectively.Likewise, as calculated from the table, in the case of red currant oil,the lower level of the amount of fatty substance by weight may becalculated as ranging from some 1.68% to 2.1% based upon the red currantoil having a γ-linolenic acid content of from 5% to 5%, respectively.The fatty sustances will advantageously be protected from oxidation bythe addition of fatty acid esters of ascorbic acid, for example,ascorbyl palmitate.

It is also possible to envisage using the fatty substances mentionedabove in animal nutrition, particularly in feeds, for example, meatcompositions for cats.

Finally, the fatty substances mentioned above may enter into thecomposition of medicaments which have a formulation adapted to themethod of administration and are administered, for example, in the formof a syrup or capsules or ocular isotonic emulsions, or they may beconstituents of the oil phase of emulsions or combined with oilsintended for parenteral nutrition, and they may represent from 5 to 80%by weight of the composition.

In every case, the pharmaceutical compositions according to the presentinvention will be stabilised physically and chemically (in particularagainst oxidation) and those for parenteral use presented in sterile,pyrogen-free form.

The present invention also relates to a process for the preparation offatty substances from pips of fruit of the Ribes genus, characterised inthat a vegetable material containing these pips is either ground andextracted by solvents or, alternatively, is pressed and/or extracted bysolvents in order to obtain a fatty substance containing at least 4% byweight of γ-linolenic acid which is practically free from the odorouscompounds, the free fatty acids, the colourings and the waxes of thesefruits.

According to the present invention, the term "vegetable material" whichis used is understood as designating the by-products which have beenmentioned above. The starting material is generally in the form ofstrongly coloured cakes containing the waxes associated with the pips,waxes and colourings representing from 5 to 7% by weight of the crudeoil which would be extracted therefrom, for example, using hexane. Thewaxes are saturated and mono-unsaturated esters of long chain fattyacids with fatty alcohols which are solid at ambient temperature. Thewaxes and colourings in question are not desired in an oil incorporatedin nutritive compositions.

A preferred starting material is the cake obtained by squeezing fruitjuices, in particular blackcurrant juice. The cake is initially dried,for example, in air for about 1 hour at about 60° C. It is coarselyground and sieved in order to obtain particles of from 1 to 1.5 mm, thesieving yield ranging from 60 to 80% by weight of the cakes. It ispossible to separate advantageously the pips from the chaff by gravityin a flow of air or by elutriation with a yield by weight of from 80 to90%.

According to a preferred embodiment of the present process, the pips arewashed with a conventional polar solvent in order to free them fromwaxes, colourings and free fatty acids. For cosmetic uses, it ispossible to use, for example methanol, isopropanol, acetone, ethanol ora mixture of these solvents, or a supercritical fluid, for example,carbon dioxide under conditions which impart thereto a polar character.For nutritional and pharmaceutical uses, a food-grade solvent will beused, for example, ethanol or supercritical carbon dioxide.

By way of example, washing is carried out by extracting the pips with apolar solvent, such as ethanol, under reflux, either in batches, forexample, at first for about 2 hours and then for about 30 to 60 minutes,or continuously for about 2 hours, then the residue is drained.

In a variant, it is possible to wash the pips using a supercriticalfluid in a polar condition, for example, carbon dioxide under from 250to 350 bars and at 60 to 80° C. in a continuous cycle, the solvent beingrecovered in gas form by lowering the pressure, then being recompressedand recycled. New it has been found that washing makes it possible toremove most of the colouring materials and the waxes present in theskins and around the pips. In effect, the waxes are precipitated oncooling from the polar solvent solution, whereas the said polar solventsolution is very strongly coloured.

A variant of the separation and cleaning of pips from the fruit juicepress cakes comprises treating the cakes enzymatically, for example,with an aqueous solution containing 0.01 to 0.5% by weight of cellulaseat a pH of from 4 to 5 and at a temperature of from 38 to 42° C. for 1to 4 hours or at ambient temperature for from 12 to 15 hours. The pipscan easily be separated from the slurry and both waxes and colouringsare at least partly eliminated in this manner.

Regardless of which variant is employed to obtain the pips, it isadvantageous to treat the washed and drained seeds with an antioxidant.This treatment protects the oil contained therein against oxidation inthe subsequent stages. Suitable antioxidants include, for example,aqueous dilute solutions of ascorbic or benzoic acids or sodium orpotassium salts of these acids, or combinations thereof, ascorbic acidbeing preferred.

The protected pips containing the antioxidant may then be pressed, forexample, in a continuous screw press at high pressure. Depending on thetype of press used, the number of pressing cycles, and the pressingconditions applied, up to 90% of the oil may be recovered.

In a variant, the pips are extracted with a solvent. Prior to solventextraction, the drained residue is ground (particles of from 100 to 300μm), from about 10 to 15% by weight of water is added, and it is thenmade into pellets or granules by extruding the paste and cutting thestrand. In a still further variant, it is possible to flake the pips ona flattening cylinder from the non-ground drained residue. These formsprevent clogging and facilitate the subsequent extraction of the oil byproviding the product with a porosity permitting a good penetration ofthe solvent, and the flakes in particular resist crushing.

A preferred variant of this stage comprises flaking the protected pipsand pressing the flakes prior to solvent extraction. The protected pipsare dried, flaked, and the flakes are preheated at a temperature of from80 to 90° C. and pressed at a pressure of from 500 to 800 kg/cm², thepress head temperature being kept under 90° C. In this way, about 50 to60% of the oil present in the pips are obtained. The resulting presscake has a density of from 0.58 to 0.65 g/cm³, about twice the densityof the flakes. This is recommended for a good percolation of thesolvent. The press cake is then milled and subjected to solventextraction.

The next stage comprises extracting the oil with a nonpolar solvent, forexample, hexane, preferably under reflux in a proportion of from 200 to250% by weight of hexane with respect to the residue. The non-polarsolvent is preferably separated from the oil by evaporation. In avariant, it is equally possible to use in this stage liquid carbondioxide or preferably supercritical carbon dioxide under conditions inwhich it is slightly polar, for example, under from 200 to 300 bars andat 40 to 60° C. Of course, it is possible to use, for example, asupercritical fluid preferably supercritical carbon dioxide in thewashing stage and in the subsequent extraction stage, or in only one ofthese stages, the other being carried out using, for example, ethanol orhexane. In the extraction stage, as above with the washing stage, thesupercritical fluid solvent is separated by recovering it in gas form bylowering the pressure and then recompressing it, and it may then berecycled.

After extraction, it is possible, although these measures are onlypreferred options, to neutralize the solution to remove the residualfree fatty acids, after having partially evaporated the solvent, forexample in the case of hexane, so that it contains about 80% to 90% byweight of solvent 10% to 20% by weight of oil, using a concentrated (2N)alkali such as. concentrated potassium or sodium hydroxide, to cool thesolution to about 0 to 4° C. for about 24 hours and to filter it at thistemperature in order to completely remove the residual waxes. Likewise,the subsequent decolorization and deodorization operations are preferredoptions: the solution is decolorized using 2 to 8% by weight of anadsorbent, for example, active carbon or activated aluminum silicatesuch as bentonite or montmorillonite with respect to the oil treated, atfrom 20 to 60° C., then the hexane is evaporated. The oil is thendeodorized by steam stripping at from 140 to 220° C. and preferably atabout 180° C. under a vacuum equal to or less than 1 torr.

According to one variant for the preparation of the oil, the pips whichhave been ground are not previously washed, but are directly extractedwith a non-polar solvent. In this case, the neutralization, the removalof the waxes by decantation, the decolorization and the deodorization asindicated above are essential for the production of a pale yellowrefined oil.

In some cases, a fatty substance is to be enriched with γ-linolenicacid. In order to do this, the oil which is freed from waxes and freefatty acids is saponified with an alkali hydroxide, for example,potassium hydroxide in a medium of methanol/water in a concentration ofabout 11%, the resulting salts are acidified using a mineral acid, forexample 2N sulphuric acid, the free fatty acids are extracted with anon-polar solvent, for example hexane, and the organic phase isseparated and dried, for example, by the addition of sodium sulphate. Ina variant, it is possible to directly treat the ground cake with analkali hydroxide, to acidify it using a mineral acid, to extract thefree fatty acids with hexane and to dry the organic phase as indicatedabove. The organic phase is fractionated by high pressure chromatographyin liquid phase, by passage over columns of silica gel loaded withsilver cations such as by utilizing silver nitrate and elutionpreferably with a mixture of dichloromethane, toluene and diethyl ether70:25:5-65:30:5 in isocratic manner, i.e., with recycling of the solventmixture of fixed composition, and a fraction containing about 60% byweight of γ-linolenic acid and about 40% of α-linolenic acid is thusobtained.

Practically pure γ-linolenic acid may be isolated from the fractionobtained from the dried organic phase by high pressure liquid phasechromatography with a C₈ or C₁₈ support in inversed phase with a solventgradient such as by a solvent mixture of acetonitrile/water,methanol/water or isopropanol/water.

The following examples illustrate the present invention. In theseExamples, the parts and percentages are based on the weight.

EXAMPLE 1

100 kg of residue obtained by the extraction of black-currant juice anddrying are treated a first time for 2 hours under reflux with 250 kg ofethanol and a second time for 1 hour under reflux with 250 kg ofethanol. The extract is drained and is dried twice at 80° C. over aperiod of 30 minutes in an air drier, and is finally ground in a hammermill.

After moistening with from 10 to 15% of water and after extruding thepaste in the form of pellets, the 89 kg of product which is obtained areextracted twice with 205 kg of hexane under reflux for 3 hours, thencooled and filtered. The hexane is then evaporated and 14.3 kg of aclear yellow oil are obtained, the weight content of free fatty acids ofwhich is 0.16%.

EXAMPLE 2

100 kg of dried residue resulting from the extraction of blackcurrantjuice are ground in a hammer mill, and the powder is sieved in order toobtain particles of from 1 to 1.5 mm with a sieving yield of from 60 to80%. The product is moistened and made into pellets and then extractedwith hexane, as in Example 1. Part of the hexane is evaporated, the freefatty acids are neutralized with a 2N solution of sodium hydroxide, theorganic phase is separated, is left to settle at 4° C. for 24 hours andis separated by filtration from the hard waxes which have settled. Theorganic phase is treated with from 2 to 8% of active carbon based on thequantity of oil in solution, then the solvent is evaporated and the oilis deodorized by stripping with steam at 180° C. under a vacuum of 0.1torr. From 13 to 16 kg of refined oil are thus obtained.

EXAMPLE 3

100 kg of dried blackcurrant pulp resulting from juice squeezing areground in a disc mill and the ground product is sieved in order toobtain 60.5 kg of particles of from 1 to 1.5 mm. The product isintroduced into an elutriator and 49.5 kg of a heavy fractionessentially comprising seeds are recovered. The fraction is washed twicewith each time 120 kg of ethanol under reflux. The process is continuedas stated in Example 1, except that two times 120 kg of ethanol are usedfor the washing operation, the dried extract is made into flakes using aflattening cylinder mill instead of the extruder, and the flakes areextracted with two times 102.5 kg of hexane. 11.1 kg of a clear, yellowoil are obtained.

EXAMPLE 4

200 kg of ethanol washed blackcurrant pips obtained as stated in Example3 are sprayed with 14 to 16 liters of water containing 30 to 50 ppm(parts per million) of ascorbic acid. The treated pips are dried atabout 70° C. for 30 to 40 min. and subsequently flaked. The flakes arethen heated in a toaster at 80 to 90° C. for 30 to 40 min. Their densityis about 0.35 g/cm³. The flakes are pressed for 30 to 50 min. in acontinuous screw press under a pressure of from 500 to 800 kg/cm², at arotational speed of the screw of 10 to 20 RPM, the press headtemperature being kept at 80 to 90° C. Under these conditions, 26 to 31kg of oil (about 50 to 60% of total oil present in the seeds) areobtained. The press cake has a density of about 0.60 g/cm³ which isquite suitable for percolation of the solvent during the subsequentsolvent extraction. It is then milled and subjected twice to hexaneextraction, as stated in Example 3, with 370 to 400 kg of hexane underreflux for 3 hours, then cooled and filtered. The hexane is thenevaporated and 22 to 26 kg of additional oil are obtained.

EXAMPLES 5 to 15: COSMETIC COMPOSITIONS

    ______________________________________                                                                % by weight                                           ______________________________________                                        5 - Care cream (water-in-oil emulsion)                                        Isopropyl myristate       30                                                  Liquid paraffin           18                                                  Blackcurrant oil          10                                                  Ozokerite                 4                                                   Magnesium lanolate        14.4                                                Lanolin alcohol           3.6                                                 Butyl hydroxy anisole (BHA) + butyl                                                                     0.01                                                hydroxy toluene (BHT)                                                         Water + preservative:quantity                                                                           100%                                                sufficient for                                                                6 - Body Milk                                                                 Liquid paraffin           8                                                   Blackcurrant oil          3                                                   Glycerol stearate         2                                                   Tween 60 (polyoxyethylene)                                                                              1                                                   (20) sorbitan monostearate                                                    Stearic acid              1.4                                                 Triethanolamine           0.7                                                 Carbopol 940 (neutralized)                                                                              0.2                                                 BHA + BHT                 0.01                                                Perfume                   1                                                   Water + preservative quantity                                                                           100%                                                sufficient for                                                                7 - Balm                                                                      Ozocerite                 4                                                   Blackcurrant oil          12                                                  Miglyol gel               30                                                  Vaseline                  20                                                  Soya oil                  15                                                  Sunflower seed oil        19                                                  8 - Body Oil                                                                  Blackcurrant oil          30                                                  Soya oil                  10                                                  Sunflower seed oil        30                                                  Peanut oil                29.8                                                BHA + BHT                 0.2                                                 9 - Face pack                                                                 Blackcurrant oil          10                                                  Cetyl alcohol             3                                                   Stearyl alcohol           3                                                   Polyoxyethylene (20) sorbitan mono-oleate                                                               4                                                   (Polysorbate 80)                                                              1,2-propylene glycol      5                                                   Glycerol                  2                                                   Titanium dioxide          3.5                                                 Preservative              0.3                                                 Distilled water, perfume concentrate                                                                    100%                                                antioxidant (BHA + BHT) quantity                                              sufficient for                                                                10 - Shaving cream                                                            Blackcurrant oil          9.4                                                 Stearic acid              7                                                   Cetyl alcohol             0.7                                                 Polyethylene glycol monostearate                                                                        3.5                                                 BHA + BHT                 0.05                                                Glycerol                  9                                                   Preservative              0.3                                                 Triethanolamine           2.7                                                 Perfume and water quantity                                                                              100%                                                sufficient for                                                                11 - Eye shadow                                                               Talc                      50                                                  Wheat starch              12                                                  Zinc stearate             3                                                   Ultramarine blue          4.5                                                 Yellow iron oxide         3.2                                                 Black iron oxide          0.5                                                 Brown iron oxide          0.8                                                 Chromium oxide            2.5                                                 Titanium mica             10                                                  Titanium mica + iron oxide                                                                              3.5                                                 Agglomerating agent       10                                                  Formula of the agglomerating agent:                                           Liquid paraffin           50                                                  Liquid lanolin            20                                                  Blackcurrant oil          20                                                  Glycerol monstearate      9                                                   Propyl parahydroxy benzoate                                                                             0.5                                                 BHA + BHT                 0.5                                                 12 - Lipstick                                                                 White base:                                                                   Petroleum ceresin         12                                                  Cadelilla wax             2                                                   Synthetic heavy esters (Croda                                                                           4                                                   Synchro wax ERLC)                                                             Castor oil                10                                                  Blackcurrant oil          15                                                  Isopropyl lanolate        15                                                  Liquid lanolin            10                                                  Acetylated lanolin        12                                                  Vaseline                  10                                                  Cetyl ricinoleate         9.8                                                 BHA + BHT (50/50)         0.2                                                 to which are added 5.4 parts by weight of the                                 following pigments for 100 parts by weight of                                 white base:                                                                   Organic and mineral pigments:                                                 Red iron oxide            1.2                                                 Titanium oxide            1.3                                                 D and C red No 9          2                                                   D and C red No 27         0.4                                                 Perfume                   0.5                                                 13 - Foundation (water-in-oil emulsion)                                       Oil phase:                                                                    Liquid paraffin           5                                                   Blackcurrant oil          5                                                   Shorea fat                4                                                   Perhydrosqualene          6                                                   Ozokerite                 2                                                   Magnesium lanolate        5                                                   Lanolin alcohol           3                                                   Iron oxide                3                                                   Titanium dioxide          4                                                   Polyethylene              10                                                  Perfume                   0.4                                                 BHA + BHT                 0.5                                                 Water + preservative: quantity                                                                          100%                                                sufficient for                                                                14 - Baby bath oil                                                            Blackcurrant oil          20                                                  Oleic alcohol polyglycol ether                                                                          15                                                  Medium chain triglycerides (C.sub.8 --C.sub.10)                                                         15                                                  Isopropyl myristate       30                                                  Octyl palmitate           10                                                  Antioxidant (BHA + BHT) and perfume:                                                                    100%                                                quantity sufficient for                                                       15 - Hair rinse                                                               The following composition is prepared:                                        Stearyl alcohol           1.8                                                 Cetylstearyl alcohol with 15 mols of E.O.*                                                              5.6                                                 Blackcurrant oil          2.5                                                 Quaternised cellulose sold under the name                                                               0.8                                                 JR 400 by Union Carbide                                                       Water quantity sufficient for                                                                           100.0% -This composition is applied after the                                 hair has been                                       washed and is left on for 5 minutes. The hair is                              then rinsed. Wet hair is easy to comb out and                                 the clean head of hair is soft and silky.                                     ______________________________________                                         *Ethylene oxide                                                          

EXAMPLES 16 TO 18: DIETETIC FOODS

    ______________________________________                                                               % by weight                                            ______________________________________                                        16 - Dressing for salads                                                      Blackcurrant oil         10                                                   Grape pip oil            14.5                                                 White vinegar            3.2                                                  Red vinegar              4.4                                                  Mustard powder           5.35                                                 Onion powder             0.25                                                 Salt                     1.4                                                  Sugar                    1                                                    Emulsifier               2.5                                                  Preservative (ascorbyl palmitate)                                                                      0.1                                                  Powdered egg             4.2                                                  Water                    53.1                                                 17 - Oil for salads                                                           Blackcurrant oil         10                                                   Grape pip oil            90                                                   18 - Infant's milk                                                            Blackcurrant oil                 0.61                                         (corresponds to 0.35% of                                                      γ-linolenic acid calculated                                             on the total weight of the                                                    fats, which is the amount in                                                                          FATS                                                  human milk)                                                                   Corn oil                         2.47                                         Lactic fat                       11.64                                        Medium chain triglycerides       9.28                                         Carbohydrates, of which 41.6 of lactose                                                                 56.9                                                and 15.3 of glucose                                                           Proteins, of which 4.4 of casein and                                                                    14.4                                                10 of lactoserum proteins                                                     Moisture                  3.0                                                 Ash, of which:            1.7                                                 Calcium                   350 × 10.sup.-3                               Phosphorus                200 × 10.sup.-3                               Potassium                 370 × 10.sup.-3                               Sodium                    103 × 10.sup.-3                               and the minimum quantities of the following                                   vitamins and trace elements:                                                  Iron                      6.0 × 10.sup. -3                              Copper                    0.3 × 10.sup.-3                               Zinc                      1.8 × 10.sup.-3                               Iodine                     25 × 10.sup.-6                               Folic acid                 80 × 10.sup.-6                               Vitamin C                 200 × 10.sup.-3                               Vitamin E                  10 × 10.sup.-3                               Vitamin B.sub.1           0.35 × 10.sup.-3                              Vitamin B.sub.2           0.5 × 10.sup.-3                               Vitamin B.sub.6           0.9 × 10.sup.-3                               Vitamin B.sub.12          1.7 × 10.sup.-3                               Vitamin PP                5.2 × 10.sup.-3                               Calcium Pantothenate      2.6 × 10.sup.-3                               ______________________________________                                         This powder is prepared as described in U.S. Pat. No. 4,216,236.         

EXAMPLES 19 TO 20: PHARMACEUTICAL COMPOSITIONS

    ______________________________________                                        19 - Capsules for oral administration                                         Gelatine capsules are prepared, containing 500 mg of                          blackcurrant oil corresponding to 80 mg of γ-linolenic                  acid per capsule.                                                             20 - Fruit syrup for internal use                                                                    % by weight                                            Blackcurrant oil       25                                                     Mixture of mono- and diglycerides                                                                    2                                                      Mixture of gums        0.7                                                    Sugar                  17                                                     Natural mixture of tocopherols                                                                       0.1                                                    (α, β, γ and δ)                                        Preservative, flavourings and water:                                                                 100%                                                   quantity sufficient for                                                       ______________________________________                                    

I claim:
 1. Food compositions for human and animal nutrition having anadded γ-linolenic acid component comprising a food containing from 0.44%[2%] to 15% by weight of an oil extracted from pips of Ribes genusfruits selected from a group consisting of Ribes nigrum, Ribes rubrum,Ribes ovacrispa, Ribes grossularia, hybrids thereof and combinationsthereof containing at least 4% by weight of γ-linolenic acid and beingsubstantially free from waxes, odorous compounds, colorings and freefatty acids for providing an equivalent of γ-linolenic acid in the foodsin an amount by weight based on the total weight of the foods whichcorresponds with an amount of γ-linolenic acid in human mother's milk byweight to 2.5% by weight.
 2. Compositions according to claim 1 whereinthe pips are pips of the fruit of Ribes nigrum.
 3. Compositionsaccording to claim 1 wherein the oil provides γ-linolenic acid in thefood in an amount of from about 0.08% [0.35%] to 2.5% by weight. 4.Compositions according to claim 1 wherein the food is an infant milkformula.
 5. The infant milk formula according to claim 4 wherein theγ-linolenic acid is in an amount of 0.35% by weight based on a totalweight of fats in the formula.
 6. Compositions according to claim 1wherein the food is selected from the group consisting of sauces,mayonnaise, dressings for salads and oils for salads.
 7. A method fornutritively supplementing foods for human and animal consumptioncomprising incorporating an oil extracted from pips of Ribes genusfruits selected from a group consisting of Ribes nigrum, Ribes rubrum,Ribes ovacrispa, Ribes grossularia, hybrids thereof and combinationsthereof containing at least 4% γ-linolenic acid and being substantiallyfree from waxes, odorous compounds, colorings and free fatty acids ofthe fruits into the foods in an amount so that the foods contain the oilin an amount of from 0.44% [2%] to 15% by weight for providing anequivalent of γ-linolenic acid in the foods in an amount by weight basedon the total weight of the nutritively supplemented foods whichcorresponds with an amount of γ-linolenic acid in human mother's milk byweight to 2.5% by weight.
 8. A method according to claim 7 furthercomprising protecting the oil from oxidation.